


First Dates

by Winchest09



Category: Supernatural
Genre: AU, Best Friends, Drama & Romance, F/M, Fluff, Fluff and Angst, Kissing, Pining, Romance, Supernatural AU - Freeform, Tooth-Rotting Fluff
Language: English
Status: Completed
Published: 2019-05-14
Updated: 2019-05-14
Packaged: 2020-03-05 13:21:51
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 6,238
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18829504
Author URL: https://archiveofourown.org/users/Winchest09/pseuds/Winchest09
Summary: Dean had watched you go on bad date after bad date, always being the one to pick up the pieces and bring a smile to your face. Always putting his own feelings for you on the back burner. Until now…





	First Dates

**Author's Note:**

> Just a fluffy little oneshot that was rolling around my mind for a while. Hope you enjoy!
> 
> \- Winchest09 xox

The sound of gentle footsteps behind him was the first thing that made Dean stop working, the smell of lunch being the second. Bringing his head up from under a rusted car hood, he wiped the oil off his hands onto the already dirty rag which had been tucked into his back pocket. Turning around, he had a brown take out bag shoved playfully into his chest.

“Order up Winchester, one mega greasy bacon big boy burger coming your way,” Y/N smiled, her lips pulling high into her cheeks as she tilted her head to one side, “with extra bacon and fries of course.”

Dean took the bag graciously before opening it up and inhaling the heavenly scent that wafted out. He too allowed his lips to break into a grin.

“Thanks sweetheart,” Dean marvelled as he began to fish out his sustenance. Before he could pull out his burger however, he noticed that Y/N was walking away and a frown creased his brow, “you not eating with me today?” he questioned across the workshop, allowing time for Y/N to turn around and answer. Dean watched as she stopped mid stride and turned to him. Her hair whisking over her shoulder as she turned her body back to face him.

“I’m not having lunch, got my big date later haven’t I?” She smiled as she shrugged slightly, “don’t want to ruin the meal by being too full.”

Dean just nodded as he let his tongue trace over his bottom lip. Truthfully, he had forgotten all about the date Y/N was due to go on.

“Oh yeah course.” Dean cleared his throat as he grabbed into his lunch, grabbing at a couple of fries, “Rich is it?”

Y/N just rolled her eyes and laughed slightly, “Rob,” she corrected.

“Ah close enough.” Dean shrugged, taking a bite out of his burger, a low rumble of pleasure resonating through is chest at how good it tasted. Y/N always knew what to get him for lunch, she always knew what extras he had and it made him smile.

She was special to him, she held a place in his heart and there were times when it killed him to see her go out on dates. Especially as she would then come to work the next morning, her mood down trodden and her eyes dull as the date had not gone the way she had thought.

“Make sure he treats you good Y/N,” Dean stated after swallowing a bite of his burger.

“…cause you’ll beat his ass if he doesn’t?” Y/N replied with an arch of her eyebrow, a smirk on her lips. Dean just stared straight back at her, his jaw ticking slightly as his face remained stern.

“Damn straight.”

“We all will, Cher.” A southern voice sounded from behind him as his friend, and colleague, Benny appeared at his side rummaging through his own lunch bag. Clearly, he had listened to part of the conversation. Dean looked to his left to see his right hand man join him, leaning his ass onto the hood of the car he’d been working on, crossing his legs to mirror Dean’s own. He gave Dean a respectful nod before diving into his own lunch, his very own burger which Dean was sure Y/N had also bought. Shaking her head at her protective colleagues, Y/N smiled.

“Thanks boys but I’m sure I’ll be fine.”

With that, she left the work shop to go back to her desk. Dean had hired her when Singer’s Auto had started to take off. The owner, Bobby Singer, had taken early retirement due to how well the business was doing and left the business in Dean’s more than capable hands. From that point on, it kept growing. Dean had hired apprentices, more mechanics and he just didn’t have the time to answer the phones and schedule appointments anymore. That’s when Y/N came in.

Dean smiled at the memory. An enthusiastic wet woman with a broken umbrella come stumbling through his office doors in the middle of a thunderstorm, a smile still on her face even though her hair now resembled tendrils and her clothes were soaked through. He had offered her a lot of paper towels and his warm jacket to which she politely declined, she just accepted the paper towels to dab her face delicately, collecting any running mascara. Dean was enamoured immediately, he didn’t have to look at her resume, her will alone to carry on without a care in the world told him she was exactly what this place needed.

“Boss, when you gonna man up and ask her out?” The southern twang shaking Dean from his reminiscing. Dean just looked to his left before going back to eating his burger.

“Shut up Benny,” Dean mumbled before taking a handful of fries. Benny just chuckled.

“Hey man, I’m just saying,” he added as his laughs died down, he too going back to his lunch before playfully elbowing Dean, “you’ve held a torch for the pretty lady since her first day here two years ago, you’ve watched her have bad date after bad date just-”

“-Dude, if you don’t mind, I’d like to stop listening to you,” Dean cut in, dramatically sighing with a roll of his eyes as he chucked the remainder of his lunch back in its bag.

The truth was a hard pill to swallow at times and Benny just loved being the one to dish it out. Benny was right when he said that Dean held a torch for Y/N but at this point, Dean was pretty sure his feelings had surpassed ‘holding a torch’. Every single time she entered the room, Dean felt like it became brighter, his air became easier to breath and his day was made with just one of her smiles. Y/N was a rarity, she didn’t cover herself in not needed makeup, and she wasn’t bothered if a speck of oil ended up on her trousers or even if she broke a nail. Hell, she even helped Dean under the hood a few times when Benny had been sick. Of course, she was just passing tools but Dean couldn’t help but answer any and all questions she had, she was naturally intrigued by what he was doing.

Dean walked away towards the office, wanting to eat the rest of his lunch in peace and quiet in his own space. Y/N being next door in the reception office had nothing to do with it. Benny just sighed as he watched Dean walk off.

“Alright man, your funeral,” he muttered under his breath.

When the end of the working day came and Dean watched Y/N say her goodbyes as she walked out to her car, he sighed a heavy sigh. He even contemplated that maybe Benny was right, maybe he should just strap on his big boy balls and ask her out. He was already dreading what mood she’d be in the next morning. If Y/N was happy, he’d have to force a smile and listen to the details. If she was sad, he’d have to force himself to not want to find the guy and break his arm for not making her feel as special as she is.

Dragging a hand down his tired face, he could only tell himself what he does every time he sees her walk away. Maybe tomorrow will be different…

The next morning, Dean followed his usual routine. Sitting on his bed nursing a cup of coffee before even contemplating moving and getting into the shower. Once dressed, he’d check in on Sammy with a quick text, grab the keys to the Impala and head off to grab breakfast for himself and Y/N, naturally.

He smiled as baby’s engine purred to life, Zeppelin playing softly on his tapes as he headed to the usual pit stop. This was a routine that started over a year ago, Y/N decided to treat him to lunch one day when he was working on a car for a single mother who had been involved in an accident. The mother hadn’t got the money to pay for two days’ worth of labour so Dean worked through his lunch to ensure it was done it one. He even stayed past the garage’s opening hours and Y/N stayed with him to keep him company.

Grabbing his order to go and placing it on the bench seat to the side of him, Dean smiled before heading off to work. As a thank you for that night, as he knew she would have been very tired the next morning, he brought her breakfast. The rest, they say is history. Each afternoon Y/N would buy him lunch and every morning Dean would buy her breakfast.

As he parked his beloved impala, he grabbed the breakfast bag and the two coffees and headed towards Y/N’s reception office. He was anxious to see her, but he looked forward to it all the same. Using his elbow on her door handle, he swung it open, making her look up from her pile of files.

“Mornin’ sweetheart,” Dean sang, closing the door behind him. “One bacon and cream cheese bagel with coffee delivered to you by your charming-” he stopped in his tracks when he saw her face. The usual bubbly smile was replaced by something a lot more forlorn. “Y/N? What’s wrong?” he asked softly, placing down her coffee and bagel on the desk, concern etched in his features.

“Oh, nothing,” Y/N shrugged, her hand automatically going for the coffee.

“Bullshit,” Dean retorted, his face stoic, a hand waving about in front of him, “was it Rich? Did he do something to you?” he pressed, edging forward ever so slightly. Y/N just snorted. 

“Rob and no, the date was…” she hesitated, trying to find the right word as she played with the lid of her coffee cup, “…ok.” Dean frowned slightly as he took the empty seat opposite her desk.

“Just ok?” he questioned, naturally curious.

“Yeah I mean, no first date is fantastic is it?” Y/N shrugged, her finger still tracing circles on the lid of her cup, her eyes focusing on the movement, “you don’t know each other, it’s awkward, you’ve got to get used to each other’s mannerisms.” Dean just scoffed slightly, taking a sip from his second coffee of the day. 

“I don’t know Y/N/N, I’ve been on some pretty good first dates,” he smirked, licking the few stranded drips of liquid from his lips.

“…that didn’t end in sex?” Y/N deadpanned, her movements stilling and her eyebrows arching in question. Dean placed a hand over his heart and feigned a hurt expression.

“Oh low blow sweetheart.”

“Sorry,” she half sighed, a smirk pulling at her own lips before she waved Dean off, “I think I’m just overthinking it.” Dean just frowned as he leaned forward in his chair.

“Overthinking it? Come on Y/N, what did he do?” he questioned, clearly concerned. He watched as you picked at the plastic bag on your desk, you were hesitating, he saw how you were rolling your tongue from one side of your mouth to the other as if you were trying to locate the words.

“…he made me pay. Not just for me but for both of us,” Y/N finally managed to get out, her voice quiet. Dean was dumbfounded and a little bit angry, he clenched his fists slightly under the desk where Y/N couldn’t see.

“He made you pay?”

“You know what, its fine. Equality and all that. He said he’d get the next one which is tonight so…” Y/N muttered, leaning forward in her chair, waving Dean off as she opened the breakfast bag in front of her.

“You’re going out with him again?” Dean interrupted, his voice coming over a tad sharp to which he saw Y/N jump slightly but her gaze never left the bag.

“Yeah I mean…he made me laugh and yeah it was awkward and stuff but tonight will be better,” she reassured herself, pulling out her bagel and setting it down in front of her, still refusing to meet Dean’s concerned gaze.

“Y/N…” Dean all but husked, worry lines creasing his brow, his hand reaching for hers across the desk but once again, she shrugged him off. Choosing to pull the bread from her bagel instead.

“No it’s fine. Life isn’t like a romantic novel is it?” she scoffed, almost trying to convince herself as she played with her food. She looked up to meet Dean’s gaze finally and she smiled a small smile. Before Dean could retaliate, she was waving him out of her room, “now go, you’ve got three oil changes and rear fender to repair today.”

“Yes ma’am,” Dean chuckled, giving her a two fingered salute from his forehead but before he could close the door, he heard her soft voice call out to him.

“Oh and thanks by the way!”

“Anytime sweetheart.” Dean rolled his head to face her and smiled as he shut Y/N’s door behind him. He couldn’t help but grip his coffee cup a little bit harder in frustration. He hated the after date morning talks and knowing that some douche bag had made her pay for the entire evening made his blood boil. He knew he had to lock himself away today, try and keep his distance away from Y/N so he didn’t say something he would regret.

It was proving to be an easier said than done task when she kept coming to him for questions on parts and appointments, seeing if he could squeeze in a service here or there. Then of course, there was lunch time where she brought him something that smelt like heaven in a bag but again she didn’t eat with him, to save room for later. Just this once, that was something Dean didn’t mind. He shared his lunch hour alone, sat in his impala with his tapes and the doors locked. He was doing anything he could to stop his mind going back to Y/N and her impending second date.

As he was trying to keep himself distracted, Dean took on more work loads and decided to stay late at the garage. All that was waiting for him was an empty apartment, a six pack of beer and some horror film re runs on the television. He wasn’t exactly dying to get home but the rumble of his stomach made him stop and look at his watch. Seeing that it was coming up to a little after nine, Dean decided to strip out of his overalls, clean up and head over to Jody’s diner for his usual Friday night takeout dinner.

Jody’s Diner was a unique place. It was classy, stylish and had more menu choices than most places Dean had been. Yet it still had that comfortable diner undertone that many people appreciated. As he made his way through the doors, he grabbed a stool at the bar and tapped his fingers against the shiny hardwood. He didn’t have to wait long before the owner herself was standing before him with a small smile.

“Hey Dean, come for your usual?” Jody smiled, her head lolling to one side as she already began to write down his order.

“Please,” he simply replied, a half smile gracing his lips as he watched her scribble on her notepad.

“Beer while you wait?” Jody asked, already popping the cap of a bottle and sliding it in front of him. Dean’s smile grew bigger as he brought the bottle neck to his lips

“Obviously,” he chided and Jody smiled, tapping his shoulder before heading to the kitchen with his order.

As he waited, Dean did his usual people watching. He spotted small families together and smiled, it was something he had hoped for one day. He spotted groups of friends hanging out, he spotted what looked like travellers who were just refuelling and then he spotted something he never expected. He spotted Y/N, on her date with the guy who made her pay for everything. He was already feeling his hold on his beer bottle tighten as he glanced their way. He noted how Rob looked sharply dressed in a suit, his jet black hair slick into place and his wrist draped in one of the biggest gold watches he’d ever seen. Dean just rolled his eyes, surely that wasn’t Y/N’s type? He took another swig from his bottle and glanced back over at her, and his breath caught in his throat. She looked beautiful.

Y/N was donned in a little black skater dress which held a square neckline and was accessorised with her favourite simple jewellery. Of course, she was wearing heels but from what Dean could see, they were reasonable. He’d have to guess kitten but then again, he was not a fashion guru. He also noted how she looked incredibly bored. He hands were placed in her lap as she was looking around the booth, she was looking anywhere but at her date.

“She’s been here for an hour and I think I’ve seen her smile once.” A voice cut through his stares as a bag was placed in front of him.

“What?” he questioned, looking back to see Jody’s warm smile coming closer to him as she leaned on her bar.

“Y/N. That’s who you’re staring at right?” Jody replied, looking towards Y/N. “If you ask me, I’d tell you that she needs rescuing. I’ve already caught him eyeing up a few of my girls,” she all but growled before she started to furiously clean glasses.

“Seriously?” Dean scoffed, his line of sight going back to Y/N and her date; an anger bubbling in the pit of his stomach. Jody just nodded as she continued to clean around her.

“Oh yeah. Donna told me that he’d slipped Claire his business card and I’ve seen him staring a bit too long at the ass of my other waitress.”

“What a dick,” Dean growled, shaking his head, he knew that Y/N deserved better.

Jody just nodded in agreement as she passed him over a six pack of beer to go with his takeout bag. With a friendly wink, Dean placed his cash on the counter top before grabbing his beer and bag to head home. As he turned off his stool, he happened to glance in Y/N’s direction once more and noticed that she had gone. He frowned slightly but when he saw that her date was still sat at the table, he figured that she had gone to the ladies to freshen herself up.

Dean swung open the front door as he made his way outside, taking a deep breath once the door closed behind him. He hesitated slightly, a fraction of him telling him to go back inside to keep an eye on Y/N as he ate his dinner, just in case her date when sour. But then he thought how weird that could come across and shook his head. Before he could take one step towards his impala, the sound of sniffling caught his attention. 

Turning to his left, he rounded the small corner to be greeted with the silhouette of a woman, leaning against the wall, and head in her hands. He recognised that figure anywhere. 

“Y/N?” he husked, slowly walking closer towards her. Y/N looked up immediately, her eyes a little wide as she furiously tried to wipe her cheeks.

“Oh…Dean, hey.”

“You alright?” Dean asked tentatively, stepping closer towards her.

“Yeah fine,” she replied quietly, crossing her arms in front of her as she leaned back against the wall, choosing to look anywhere but at Dean.

Dean pursed his lips a little and nodded slightly, taking note of her defensive stance. He walked to the side of her and he too leaned his back against cold wall, crossing one foot over the other as he placed his six pack on the ground. He waited for a couple of minutes for her to move, for her to say something but all she did was rub at her arms in a comforting manner as she tried to control her snuffles. Deciding that enough time had passed, he decided to speak up.

“You know, I’m no expert but I’m pretty sure on a second date you’re not meant to be standing out here alone,” he muttered softly, trying hard to not let his feelings about her date be mirrored through his words. Y/N just pushed herself off the wall and walked forward a few steps, gently kicking at a stray stone on the floor.

“I just needed some fresh air.”

“Come on Y/N, this is me you’re talking to,” he sighed as he too pushed himself off the wall. “Jody told me she’s only seen you smile once on this date.”

“That’s what she said?” Y/N snapped, her head whisking around, her hair following. Dean just nodded as he saw the fury in her eyes. “Yeah well, she owns the bar, she’s not gonna be looking at me the whole time is she?” she spat defensively. Immediately Dean held his hands up in surrender, his take out bag bashing into his side as it swayed with the movement.

“Hey, woah, don’t shoot the messenger.”

“I’m sorry I just-” Y/N sighed, running her hands through her hair, “I thought this was it you know? But again, here I am, alone in the dark. Not that it matters to Rob in there because he’s just interested in anything with a low cut cleavage and a hole between their legs,” she scoffed, her hand gesturing towards the diner. “Also, do you know what that douche did? As he was paying he ordered me a salad. A fucking salad,” she bellowed, her arms flapping to her sides. Dean just nodded and grimaced slightly.

“Yeah…Jody told me about the girls. The salad, well that’s just damn wrong.” With that, he saw how Y/N’s shoulders sagged slightly, her posture resonating defeat.

“I don’t know why I bother De,” she muttered quietly, looking at him with glassed over eyes.

Dean’s heart broke at the sight of her standing there. She looked incredible yet she was being treated like she was nothing. To him, she was everything. In that one moment, Dean had two options. He could go into the diner and tell her date what a piece of shit he was and make a scene or, he could finally grab those big boy balls and show her what a date is meant to be like. Sure, he wasn’t dressed to the nines and probably still smelt like motor oil but in that moment, all he cared about was ensuring Y/N was happy. He wanted to put a smile back onto her beautiful face. Swallowing hard, Dean took a step closer to her.

“Hey, can I ask you something?” His voice was gruff with nerves. He watched as Y/N nods, tucking some hair behind her ear. Taking a deep breath and wiping his free hand on his jeans, he ticked his jaw. He was smiling a nervous smile, his gaze flickering between Y/N and his boots. “Do you wanna come on a date with me?” he asked, the question sounding more confident to her than it did to him. Y/N’s face changed immediately to one of shock and Dean didn’t know if he had just ruined everything.

 

“You…you want to take me on a date?” she stuttered, struggling to repeat the sentence as a smile pulled at the edge of her lips. Dean noticed and he smiled a genuine smile back at her in relief.

“I’d love too,” he husked, walking closer towards her.

“…now?” Y/N questioned, pointing to the ground with one eyebrow arched. Dean nodded, a small laugh escaping his lips as he rubbed at the back of his neck with nerves.

“You look incredible Y/N, the night is young and I have a bag full of Jody’s best takeout food.” He held up the bag in front of her, swinging it slightly to which she rolled her eyes playfully. “Let me show you what a first date should be,” he all but whispered as he held out his hand to her. Y/N lips broke out into a wide grin as she entwined her fingers with his own.

“You had me with the takeout.”

“Atta girl,” Dean praised as he placed a kiss to the back of her hand. He leaned down to pick up the six pack of beer after looping the plastic handles around his wrist and led her to the Impala. He’d waited two years to hold her hand like this and he’d be damned if he was giving it up for a pack of beer.

Holding the passenger door open for her, Y/N smiled as she slid in onto his leather seats. Dean’s stomach was flipping like crazy, he couldn’t believe this moment was actually going to happen. Gently shutting the door, he made his way around the front of the impala to the driver’s side. Settling himself behind the wheel, he placed the six pack and take out in the middle of the seat and let the engine of his beloved baby roar to life.

He didn’t even need to plan where he was going to take Y/N on the first date, for he had had it planned in his head for a very long time. They drove in a comfortable silence, the hum of Dean’s tapes providing the soundtrack to their journey as they travelled to Deans chosen destination. He looked over at her every now and again and saw how she was leaning her head on her hand, looking out of the window. A soft smile was on her face as the warm wind blew over her face and through her hair through the tiny gap she had created when she wound down her window.

Dean gripped tightly to the steering wheel, he was overwhelmed with emotions. He was happy, nervous, lustful, all rolled into one. He licked at his lips, his mouth becoming dry each time he tried to strike up a conversation with her. But his nerves? His nerves were telling him to not blow it. This was his one chance to have everything he had wanted for two years.

The asphalt turned into dirt and gravel as Dean took a turn into the National Park. The sign big and illuminated with hanging yellow lights as he took the trail up high to the peak of the mountains. Naturally, he couldn’t drive to the highest point but he did drive as far as the terrain would allow and put the impala in park. He saw how Y/N’s body language immediately changed. She leaned forward onto the dash, her eyes scanning everything they possibly could.

Where Dean had parked was on a hillside overlooking miles of fields, forests and a big lake in the middle. Rivers led off the lake, snaking their way through the countryside and forests. The night sky was impeccably clear, giving the best view too all of the stars that shone that night. The view was breath taking.

Dean took a moment to study her as she looked around. He noted how her eyes were lighting up at everything that was around her and it made him smile. So far, so good.

Getting out of the car, he made his way around to her side and held open the door for her, offering his hand to steady her feet. He felt his skin tingle when she slid her hand into his, a spark of electricity jolting through his arm. She blushed slightly and it made Dean wonder if she had felt it too. Hand in hand, he guided her to the front of the Impala, encouraging her to jump up into the hood as he softly patted the metal. Y/N stopped, her eyes wide as she shook her head slightly.

“De, I…I don’t want to scratch her paint,” she confessed and if it was possible, Dean swore in that moment she had captured more of his heart. Dean just smiled widely back at her, tapping the Impala’s hood once again.

“Baby’s tougher than she looks sweetheart.” He saw however that Y/N was not moving from her spot, still shaking her head as she let go of his hand.

“No…let me take my heels off,” she insisted, leaning on Dean as she lifted her leg up to slip off her shoes. She placed them together neatly next to the impalas front wheels before turning back to Dean.

“You ready?” he asked, coming to stand in front of her as the back of her thighs touched the hood of the impala.

All she did was nod. Dean didn’t notice how her skin was covered in goose bumps when he gently caressed the back of her hand, he didn’t notice how her lips became flush when he placed both of his large hands on either hip. With the greatest of ease, Dean lifted Y/N onto the hood of the impala and assisted her in leaning back onto the windshield.

Quickly grabbing the food and the beer, Dean too hopped onto the hood of his car and took his place at Y/N’s side. Rustling through the plastic bag, Dean pulled out carton after carton.

“Ok so, on the menu we have fries, hot wings and BBQ ribs,” he announced, opening the carton and handing Y/N some napkins before popping open a bottle of beer, “complimented by El Sol,” he continued, handing her the bottle beverage. Y/N took it gratefully with a beaming smile.

“Sounds wonderful.”

“Ladies first,” he encouraged, nudging at the open cartons between them.

Y/N glowed with happiness, Dean knew how much she loved her food, and salads were not going to cut it. She picked at a few fries before going for a couple of the BBQ ribs, placing them on her napkin in her lap.

Dean grabbed a few wings for himself, a handful of fries and just the one rib. He knew that over everything he’d bought, she’d favour those the most. As he bit into his wing, he nearly choked on the meat as he heard a moan come from the side of him.

He played it off as a cough and took a swig of his beer as he noticed Y/N with the ribs in her hands, eyes closed as she savoured the flavour.

“Oh my god this is heaven,” she almost purred.

“I’m glad…glad you like it,” Dean stuttered, trying to get a hold on his words. The way Y/N was licking at her lips and fingers were igniting thoughts in Dean that were sinful. He knew he had to bring up a new subject of conversation, he had to divert his gaze away from her tongue running along her bottom lip as she licked at some left over sauce.

“Like it?” Y/N laughed as she placed the bone of her rib into her napkin, “this, this is food of the gods right here.” Dean just nodded as he continued eating his wings.

“Jody does good food.”

Y/N nodded in agreement as she sipped on her beer. There was a moment of silence as they both continued eating their food, taking in the scenery around them before they made idle chit chat amongst themselves. Little topics like breakfast came up, Dean’s favourite dinner that Y/N had bought him and remember the pranks they had both pulled on Benny.

If an outsider looked in on this scene, you’d think that Dean and Y/N had been together a couple for years as the conversation flowed effortlessly between them. No awkward silences, belly aching laughter with lingering glances and touches.

As they finished their food, Dean hopped off the hood to clean up, placing the rubbish back into the plastic bag and into the back seat of his car. As he was coming back around to join Y/N’s side once more, he noticed how she shivered slightly as she looked over the lake, rubbing at the tops of her arms. Dean didn’t even hesitate, he shrugged off his black cotton jacket and hopped back onto the hood. Shuffling closer to her, he placed his large hand behind her back, gently pushing her forward.

“Hey, lean forward sweetheart,” he spoke softly as he looked into her Y/E/C eyes.

“Why?” she frowned slightly, her arms still crossed over her bare skin as she obeyed his request. Dean watched how her gaze wandered down to his jacket that he was currently ensuring was the right way around.

“You’re cold,” he stated as he moved closer towards her. 

“De…” She whispered, her eyes slightly widening at his gesture. Dean himself was only left in a black Henley and he knew that she would be worrying about him being cold too in that moment. He smiled at the thought, he loved how she was so caring about others. Always wanting to put everyone else before herself.

“Shush, you’re cold,“ he chided, a smirk on his lips as he wrapped his jacket around her shoulders.

Dean could feel her gaze on him as he ensured she was securely snug in his clothing, gently pulling her hair out of the collar as she held onto the lapels of the jacket. The air suddenly changed around him, he felt like it had become thick and he couldn’t breathe. He saw her in the peripherals of his vision, inhale his scent from the collar. It made him hard to swallow. He brought his hands down and pulled the middle of each side of the jacket inward before looking back up and meeting Y/N’s gaze.

“It…it looks good on you,” he stuttered, his hands still on the jacket as he gazed into her eyes. He felt the tips of his ears turn pink under her stare but with his compliment, he saw how she too blushed.

“Thank you,” she whispered, breaking his gaze and looking down at his hands, her hair falling in front of her face. Before she could contemplate tucking it behind her ear, she felt a warm hand caress her cheek. Dean had let go of his jacket and was currently using one of his warm hands to tuck her hair behind her ear. His fingers tracing the edge of her jaw as he tilted Y/N’s face up to meet his eyes once more.

“Don’t hide that pretty face from me sweetheart,” he husked, his thumb coming around to trace the edge of her bottom lip. This was it, he thought. It was now or never. There was barely any space between them as it was but Dean bowed his head closer to hers.

“You think I’m pretty?” Y/N whispered, her eyes scanning his for any signs of deceit but she found nothing but endearment. The way Dean was looking at her, was enough to fuel her dreams for the next few years.

“Sweetheart,” the nickname rumbled from his chest as he leaned forward to rest his forehead on hers. “You’re breathtakingly beautiful.”

 

He heard Y/N gasp at his confession and watched as her eyes danced down to his lips. He wasted no time, he’d waited two years for this moment, and he wanted it to be perfect. His thumb was still tracing her bottom lip as he pulled her in close to him, his lips matching hers in perfect harmony.

In that single movement, Dean felt like the world had stopped turning. Everything around him didn’t matter. The only thing that mattered in that moment was the incredible woman that was in his arms. He allowed his large hand to caress her cheek as his plump lips massaged her own, both of them kissing with a passion that had been ignited that evening. He gently traced his tongue along her lower lip to which Y/N moaned and granted him access. Dean’s coat had long been forgotten as Y/N’s hands were pressed flat against his firm chest.

Dean was sure that she would be able to feel his heartbeat doing overtime as he felt like it was going to bust out of his chest any second. The tiny moans Y/N was making, the tender touches, the way she angled her face so Dean could take in all of her. He pulled her closer to him, ensuring her chest was flush with his as his free hand and arm was cradling her back.

“God damn Y/N,” Dean growled against her lips. She just smiled as she pulled back slightly, running her hand softly down Dean’s chiselled jawline.

“This is one hell of a first date Winchester,” she whispered as she kissed the edges of his mouth. Dean let a rumble erupt from his chest, his hands spread flat against her back, pulling her impossibly close to him, brushing his lips against hers.

“You just wait until the second.”


End file.
